A kind of phosphono-substituted methanol derivative and its preparation method and application
A derivative and phosphono-based technology, applied in the field of preparation of organic compounds, can solve the problems of increased storage difficulty and cost, operator and environmental damage, aldehyde irritating taste, etc. Small, Inexpensive Effects
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Embodiment 1
[0033] Embodiment one: the synthesis of diphenoxyphosphinyl benzyl alcohol
[0034] With benzyl alcohol and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0035] Add benzyl alcohol (0.054 g, 0.5 mmol), diphenylphosphine oxide (0.101 g, 0.5 mmol), potassium persulfate (0.270 g, 1.0 mmol) and methanol (2 mL) into the reaction flask, and react at room temperature;
[0036] TLC tracking reaction until complete completion;
[0037] The crude product obtained after the reaction was separated by column chromatography (dichloromethane:methanol=40:1) to obtain the target product (yield 76%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 7.97 - 7.72 (m, 4H), 7.64 - 7.37 (m, 6H), 7.34 - 7.09 (m, 5H), 6.55 (d, J = 17.1 Hz, 1H),5.64 (s, 1H). As a ligand, the product can be used in the formylation reaction of alkenes in industrial production.
Embodiment 2
[0038] Embodiment two: the synthesis of diphenoxyphosphinyl (2-chlorophenyl) methanol
[0039] With 2-chlorobenzyl alcohol and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0040] Add 2-chlorobenzyl alcohol (0.143 g, 1.0 mmol), diphenylphosphine oxide (0.101 g, 0.5 mmol), potassium persulfate (0.270 g, 1.0 mmol) and ethanol (2 mL) into the reaction flask, 30 °C reaction;
[0041] TLC tracking reaction until complete completion;
[0042] The crude product obtained after the reaction was separated by column chromatography (dichloromethane:methanol=40:1) to obtain the target product (yield 73%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 7.81 (dd, J = 11.2,7.7 Hz, 2H), 7.74 (dd, J = 11.5, 7.7 Hz, 2H), 7.64 – 7.44 (m, 6H), 7.35 –7.14 (m, 4H), 6.70 (dd, J = 18.3, 5.8 Hz, 1H), 5.96 (t, J = 6.1 Hz, 1H).
Embodiment 3
[0043] Embodiment three: the synthesis of diphenoxyphosphinyl (3-chlorophenyl) methanol
[0044] With 3-chlorobenzyl alcohol and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0045] Add 3-chlorobenzyl alcohol (0.214 g, 1.5 mmol), diphenylphosphine oxide (0.101 g, 0.5 mmol), potassium persulfate (0.270 g, 1.0 mmol) and water (2 mL) into the reaction flask, at 40 °C reaction;
[0046] TLC tracking reaction until complete completion;
[0047] The crude product obtained after the reaction was separated by column chromatography (dichloromethane:methanol=40:1) to obtain the target product (yield 75%). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 7.91 – 7.75 (m,4H), 7.64 – 7.44 (m, 6H), 7.36 – 7.12 (m, 4H), 6.65 (dt, J = 24.7, 12.3 Hz,1H), 5.70 (t, J = 6.7 Hz, 1H).
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